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<h1><a href="https://archiveofourown.org/works/28001121">Truth Is For Sissies</a> by <a class='authorlink' href='https://archiveofourown.org/users/11paruline44/pseuds/11paruline44'>11paruline44</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Birthday, Castiel and Dean Winchester Need to Use Their Words, Dean Winchester is Bad at Feelings, Fluff, Gen, I don't think this is crack considering what actually happens in this show but I could be wrong, I swear, Kevin Tran is So Done, Kevin Tran's stank-ass boat, M/M, Sassy Sam Winchester, Season/Series 08, Truth or Dare, and then some purely accidental angst comes in, it gets resolved, omg I love all of these tags hahahaha, wow I love how that's a tag</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-12-11</td></tr>

<tr><td><b>Updated:</b></td><td>2020-12-11</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-18 10:49:21</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>6,789</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/28001121</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/11paruline44/pseuds/11paruline44</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Dean discovers that it's Kevin Tran's birthday—and he knows exactly what the poor kid needs. A proper, juvenile, rip-roaring game of Truth or Dare. What could go wrong?</p><p>Cas is confused. Kevin is a little shit. Sam's going to get Dean to choose "Truth" before the night's out, if it's the last thing he does...</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>pre-Castiel/Dean Winchester - Relationship</td></tr>

<tr><td><b>Comments:</b></td><td>6</td></tr>

<tr><td><b>Kudos:</b></td><td>119</td></tr>

</table>

<a name="section0001"><h2>Truth Is For Sissies</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>I have no self-control, I swear. My WIPs are all so disappointed in me... but when the inspiration strikes, you know?</p><p>This takes place roughly in the first half of Season 8 after Hunteri Heroici (E8), because Season 8 disappointed me and I felt like spicing it up. Though, honestly, S8 is a breath of fresh air compared to the series finale, right? Heh, heh... *cries*</p><p>I tried to keep this out of the realm of crack territory, so unfortunately, Team Free Will is still a little emotionally constipated as in canon... but they still get to be happy, I swear.</p><p>Oh, and, happy late birthday, Kevin!</p>
    </blockquote></div><div class="userstuff module">
    
    <p>“You’re kidding,” Dean says, interrupting the kid’s tirade.</p><p>“No, I’m not!” Kevin shouts, waving his hands in a tired, exasperated sort of anger. “It’s my birthday, and no, I’m not trying to get out of tablet duty, since it’s not like any of Crowley’s demons are going to take a pause for me, but if I could have some goddamn empathy for one freaking moment—”</p><p>“Wait wait wait, hold on, kid,” Dean juts in again, holding his hands up in what he hopes is a placating gesture. “Why didn’t you say so earlier?”</p><p>Kevin stares at him. He’s still evidently all worked up, but there’s disbelief mingling in his expression now, as if he didn’t expect Dean to care. “What?”</p><p>Dean feels a twist in his gut. It’s true that he and Sam haven’t really dropped into Kevin’s neck of the woods for much more than information for a while—but they’ve all been a little busy, what with how the world’s decided to settle in a neverending state of there’s-an-apocalypse-imminent-and-only-the-Winchesters-care-enough-and/or-are-stupid-enough-to-try-and-stop-it. But… just because he and Sammy have never been big on holidays, thanks to growing up in The Life, doesn’t mean that other people are like that. He scans Kevin’s messy, decrepit boat, the blood-painted wards, the scattered papers, the crusts of dirt, the meager fridge. A year ago, this kid had a family, a white picket fence, the whole shebang. Before Dean, you know, ruined his life. Or, as Sam would have been quick to point out, Dick Roman digging up the Leviathan tablet and Crowley and his demons ruined Kevin’s life, but of course Dean still feels responsible. </p><p>Coming to a decision, Dean takes his phone out of his pocket and dials up Sammy. Before the call connects, Dean asks Kevin, “What kind of cake do you like?”</p><p>Kevin does a double take. “Cake?”</p><p>Just then, Sam picks up. “Dean, what now?”</p><p>“Sammy, you’ll never guess what.”</p><p>There’s a pause, which Dean knows would have been filled by a bitchface if Sam were in the room. “What,” he says, voice flat.</p><p>“Apparently, it’s Kevin’s birthday, which he never thought to tell us.” Kevin frowns at this, and naturally, Dean ignores him.</p><p>Even over the phone, Dean can feel Sam’s demeanor shift. “Really?” he replies.</p><p>“Yeah, so, if you and Cas aren’t done with the grocery shopping, the birthday boy could use some cake.”</p><p>“Oh, well, you just caught us in time. I’d be happy to—wait, hold on,” Sam says, and there’s a series of staticky scratches and bumps. “Cas!” Sam’s voice, fainter, shouts. “<em>Cas!</em> Don’t—” the phone picks up yet another round of white noise, and Dean grins. Oh, man, it sounds like Cas just got himself into some of his patented angel your-human-customs-puzzle-me trouble. Dean suddenly wishes he’d gone on the boring grocery run after all.</p><p>Presently, Sam’s voice comes back on the line. “Sorry,” he says, sounding like he’s holding back laughter. “Cas, uh, tried to talk to the lobsters.”</p><p>Dean blinks. “The <em>lobsters</em>?”</p><p>“You heard me. Things… escalated a bit.”</p><p>Dean bursts out laughing. Kevin gives him a half-annoyed <em>what?</em> look, but Dean can’t find it in him to be embarrassed. “Oh man. Oh <em>man.</em> First that cat, and now <em>lobsters?</em> Dude’s gonna go full Snow White on us one of these days.”</p><p>“I can hear you, Dean,” Cas’s faint but clearly unimpressed voice filters through the line.</p><p>Sam clears his throat. “Anyway… cake? Did Kevin specify what kind yet?”</p><p>“Hold a sec,” Dean says, and then cups the phone to his shoulder. “Hey Kev, I’m serious about the cake. What kind do you like?”</p><p>Kevin stares for a moment more, and then his shoulders relax. “Uh, carrot cake.”</p><p>Dean starts to chuckle, but Kevin’s face remains stoic. <em>Wait, wait, hold up.</em> Dean tries not to screw his face up in revulsion. “Carrot cake. You’re serious.”</p><p>Kevin gives him an I’m-too-tired-for-this-shit bitchface worthy of Sam. “Yes.”</p><p>Dean gives himself an inward shake. It’s the kid’s day, he gets what he wants. He brings the phone back up to his ear. “‘Well, Sammy, it’s your lucky day. Kid wants rabbit food. <em>Carrot cake.”</em></p><p>“Wait, seriously?” Sam sounds suitably incredulous.</p><p>“Yep, you heard me right,” Dean grins, and Kevin sighs.</p><p>“Well, alright then,” Sam says. “One carrot cake, coming right up.”</p><p>“Awesome. Oh, and don’t forget to stock up on the booze. We’re celebrating.”</p><p>“Oh, don’t worry, I already had that covered,” Sam says in a tone of voice that makes it clear he’s rolling his eyes. </p><p>“Just checking,” Dean says, and he hangs up. He turns to face Kevin, who still looks skeptical. “Well,” he starts, rubbing his hands together. “The demons can wait for a night. We’re doing your birthday <em>right,</em> Kevin.”</p><p>Kevin has the good sense to look a little terrified.</p><p>***</p><p>The carrot cake isn’t as bad as he thought it would be, all things considered—though, maybe that’s just because he washed it down with copious amounts of beer. But, anyway, they’ve finished the cake and the happy-birthday-to-you part, and it’s only seven o’clock. Which means, now the real fun can begin. </p><p>Dean rises to his feet and claps his hands. “Alright! Let’s get this party started!”</p><p>Sam raises an eyebrow, and Kevin gives him a look full of apprehension. “I don’t know if you’ve noticed, but there are only four of us, and we’re hiding out in an old demon-proof boat. Not exactly party material.”</p><p>Dean sighs. “Four’s a good-sized crowd in our line of work. Besides, I’d say we’re all more than enough fun to make a good party. Isn’t that right, Cas?” he says, leaning over to give Cas a friendly pat on the shoulder.</p><p>Cas tilts his head, looking skeptical, which is exactly what Dean was fishing for. He grins.</p><p>“Dean,” Sam sighs. “You’ve been working up to something all afternoon. What is it?”</p><p>“Glad you asked, Sammy,” Dean says with gusto, and he places one foot on his chair in a dramatic gesture. “We’re playing Truth or Dare!”</p><p>There’s silence for a moment. Then, Kevin pushes his chair back, eyes wide. “Oh, no way. No no no no no.”</p><p>Sam frowns. “Dean, isn’t that a little… juvenile?”</p><p>Dean huffs. Honestly. Sammy has no sense of fun, sometimes. “That’s the point, Sam. Kid’s a teenager. Truth or Dare is what any self-respecting drunk teenagers do on their birthdays. We’re giving him the full experience.”</p><p>“What’s… Truth or Dare?” Cas asks, enunciating each word slowly. </p><p>Dean smirks at the perfect timing, and gestures at Cas. “Plus, we get to teach him. All humans play Truth or Dare at least once.”</p><p>“The answer’s still no,” Kevin juts in, shaking his head. </p><p>“Come on, Kevin,” Dean says, turning back to him. “I know you’ve been a little mad at us, and, uh, you probably have good reason to.” He leans his elbows on the table, looking Kevin in the eye. “Don’t you think this is the perfect opportunity for some payback?”</p><p>Kevin narrows his eyes. For a moment, Dean’s confidence wavers, but then Kevin’s eyes harden, and he can see the exact moment the kid concedes. “Fine. I’m in.”</p><p>Dean gives him a victorious smile and straightens. He turns to Sam, who still looks distinctly un-excited. “There you have it.”</p><p>“I still don’t understand,” Cas says.</p><p>Sam sighs, taking a long gulp of beer. “It’s a game,” he explains.</p><p>“It’s like how it sounds,” Dean continues. “Kev here will start, since he’s the birthday boy, and he gets to ask one of us Truth or Dare. If you pick Truth, you’ve got to answer any one question he asks you truthfully, and if he picks dare, you have to do any one thing he asks you to.”</p><p>Cas is still frowning. “Why would you purposefully let anyone—”</p><p>“Dares are supposed to be jokes,” Sam says. “Usually, they’re supposed to be something you’d normally never do, but would be funny for everyone else watching you.”</p><p>Cas squints. “I… see,” he says, though it’s obvious he doesn’t.</p><p>“You’ll get the hang of it as you watch,” Dean says, though he actually has no idea if Cas will. That’s part of what will make this so entertaining. But, anyway… “If there’s a truth or a dare that you won’t do, you are allowed to switch to the other option. But, in this house, no takebacks. Once you decline the truth, you <em>have</em> to take the dare.”</p><p>“And vice versa,” Sam points out. </p><p>Dean nods. “Right.”</p><p>Sam rolls his eyes. “Honestly, Dean. I’m surprised you’re even explaining the truth part. Truth or Dare with you always just ends up as ‘Dare.’”</p><p>“Well, Truth <em>is</em> for sissies,” Dean agrees, and Sam gives him a withering bitchface. “But I’m explaining the whole thing for Cas’s benefit, just in case.”</p><p>“I think you don’t like Truth just because you’re afraid of it more,” Sam fires back, the corner of his mouth quirking upward.</p><p>Dean feels a flare of righteous indignation at this—but, secretly, he can’t argue, and Sam knows he can’t, so he settles for griping, “Shut up, bitch.”</p><p>“Jerk.”</p><p>Kevin clears his throat. “Are we good now? Can we get started here?” Dean turns back to the Prophet of the Lord. There’s an anticipatory gleam in his eye, one Dean’s never seen before, and he grins inwardly. Kid’s getting a backbone. This is going to be fun.</p><p>“Yup,” Dean says, settling back down into his chair. “Fire away, tiger.”</p><p>“Alright,” Kevin smiles, and, like Dean predicted, fixes Dean in the eye. “Dean. Truth or Dare.”</p><p>“Dare,” is his automatic response. He takes a swig of beer as preparation.</p><p>“Cool,” Kevin replies. “I dare you to eat one full frozen hot dog straight from the freezer.”</p><p>Dean raises an eyebrow. “That’s it?”</p><p>Kevin juts his chin out. “I’m just warming up.”</p><p><em>Sure,</em> Dean thinks, but he leaves it at that and makes his way towards the freezer. Soon enough, he’s back at the table, frozen hot dog in his hand, and he jams the end in his mouth. He tries to bite down, but his teeth glance off—the thing’s as frozen as a rock. He tries not to show his discomfort, but from the look on Sam and Kevin’s faces, it doesn’t work. Dean settles for sucking on the hot dog to warm it up. <em>Just pretend it’s a popsicle. A… meaty popsicle.</em></p><p>Cas chooses this moment to pipe up. “I thought humans preferred food they can bite into.”</p><p>Dean glares at him. </p><p>“That’s the point. It’s supposed to be awful,” Kevin explains.</p><p>Cas leans back in his chair, watching Dean with a contemplative look. “Ah,” he says.</p><p>“Alright,” Dean says, a little too loudly, his mouth still full of meat popsicle. “Sam. Truth or Dare.”</p><p>Sam pauses, his eyes narrowing at Dean. After a beat, he decides. “Truth.”</p><p>Dean rolls his eyes. “Lame, Sammy.” He tries to punctuate his point by gnawing off his first bite of the hot dog, but five seconds and a full set of numb teeth later, he gives up, much to Kevin’s evident delight. The little shit.</p><p>“Okay, then,” Dean starts. He has to think for a moment, but then his twisted noggin delivers. “Who would you rather do: Dick Roman,” he lets that sink in, watching Sam’s growing bitchface, “or… Bobby.”</p><p>Sam’s face is priceless. “Ugh! Dude, come on.”</p><p>“Truth!” Dean repeats.</p><p>“Jerk,” Sam mutters. He downs some more of his beer.</p><p>Cas tilts his head. “By ‘do,’ do you mean… have sexual intercourse with?”</p><p>Dean guffaws and pats Cas on the back. “There you go, buddy, you’re getting it!”</p><p>Cas looks like he doesn’t know whether to be appalled or amused. Dean just smiles and makes another attempt at taking his first bite of hot dog, which is finally successful.</p><p>“Okay,” Sam says, face full of defeat. “I’d choose Dick.”</p><p>“Hear that, boys? Sammy’s gonna get some Dick!” Dean crows, wiggling his eyebrows.</p><p>Sam just sits back and stares at the ceiling. “You just wanted to say that sentence, didn’t you,” he grumbles. “Knew that was coming.”</p><p>Dean only laughs. </p><p>“Real mature,” Kevin comments, but he’s smiling anyway. It’s an expression Dean hasn’t seen on the kid’s face in a long time. A pang of guilt lurches in his stomach, and he bites down harder on his frozen hot dog.</p><p>“Okay…” Sam starts, scanning the table for a new victim. “Uh, Cas? Truth or Dare.”</p><p>Sam’s probably trying to make sure Cas feels included. Thoughtful, but he’s probably also going to go easy on the guy to start him out. Boring.</p><p>Cas takes so long to respond Dean starts to wonder if he has to re-explain the rules, but then he says, “Dare.”</p><p>Dean feels his eyebrows rise. Well. That wasn’t what he was expecting.</p><p>From the look on Sam’s face, it wasn’t what he was expecting, either, but Sam takes it in stride. “Hmmm… alright, I dare you to bring us a pair of Vladimir Putin’s underwear.”</p><p>Dean nearly chokes on his hot dog. Sammy, the mad genius. If the dude’s got crazy angel mojo, might as well make use of it.</p><p>Cas just stares. “What… purpose does that serve?”</p><p>Kevin bursts out laughing.</p><p>“Cas, you’ll be doing us all a favor. Everybody hates Putin. Now, we’ll have our own little trophy of his.”</p><p>Cas looks pensive for a moment, then smiles. “Oh, I see. To you, underwear is an intimate item meant not to be seen, so possessing that of another is a symbol of their shame.”</p><p>“Sure, Cas,” Dean says, trying hard not to laugh.</p><p>“Okay,” Cas nods. Then, he disappears. </p><p>Several minutes pass by. Dean sips his beer and tries to make some headway on his hot dog. The room is alternately filled with anticipation and stifled giggles. Finally, Cas reappears, and—he’s got the goods. Dean’s slightly disappointed when he sees them—navy blue boxers, they look pretty normal—but Cas is still just standing there, stiffly holding a pair of Vladimir Putin’s underwear, and Dean can’t help it. He cracks up.</p><p>“Oh my <em>God,”</em> Kevin snorts.</p><p>“Uh… you don’t have to keep holding them,” Sam says.</p><p>“Here, let me,” Dean buts in, and he takes the underwear from Cas’s hand. Good Lord, he’s holding Vladimir Putin’s boxers. Oh man, this is not going to be old soon.</p><p>“These are keepers,” he announces, proud, and goes to put them on the table.</p><p>“Whoa whoa whoa, no. Keep those things off my stuff.” Kevin stands abruptly, placing a protective hand over his (very dirty, Dean might add) table.</p><p>“Geez, don’t get your panties in a twist,” Dean goads, but finally plops them down on the floor next to his duffle. They aren’t touching his things, but it’s a reminder to bring them with when they go. Maybe mount them on the wall of the Bunker.</p><p>“Alright, Cas, it’s your turn,” Sam prods.</p><p>“Right,” Cas says. Dean expects him to spend a while deciding, but he gets right to the point. “Dean. Truth or Dare.”</p><p>Dean raises his eyebrows. This should be interesting. “Dare.”</p><p>Cas eyes him. “I… dare you… to sing a Led Zeppelin song.”</p><p>Dean doesn’t know whether to be disappointed that Cas didn’t really get it… or secretly amused. Ah well, first try. “Uh… you sure, buddy? I don’t think that’ll be… too embarrassing for me.”</p><p>“You sure about that?” Sam mutters, and Dean shoots him a look.</p><p>Cas just keeps gazing at him. If he were more into human gestures, Dean guesses he might have shrugged. “You do not do it very often, and it is enjoyable.”</p><p>Dean looks away, finding it suddenly too hard to meet Cas’s eyes. “Alright. Black Dog, Sammy,” he says, and Sam starts pulling up the track on his laptop. “Let’s hit it.”</p><p>***</p><p>“Truth or Dare, Kevin.”</p><p>“Truth,” comes the answer. Dean was expecting it, but it’s still disappointing.</p><p>“Aw, come on, man!”</p><p>Kevin makes a get-on-with-it gesture.</p><p>“Alright…” Well… he can still torture the kid without making him wear Putin’s undies, like he planned. “Who would you do? Me or Sammy?”</p><p>Kevin’s responding glare is downright bone-chilling.</p><p>***</p><p>The very next round, Sam beats him to the punch, and it’s Dean who has to wear the Putin undies. Dean’s supposed to be embarrassed, but mostly, he’s just proud.</p><p>***</p><p>“Castiel,” Kevin says. “Truth or Dare.”</p><p>“Truth.”</p><p>Kevin frowns. “Um… oh, I know. Luke. Dean said you mentioned something about his life sucking.” Dean stifles a groan. Crap. He knows where this is going. “So. What was Luke’s life like?”</p><p>“Long and ignominious,” Cas replies without missing a beat, and Dean almost snorts.</p><p>“Was it worse than mine?” Kevin prods. He’s trying to keep cool, but there’s a sort of desperate determination beneath the surface.</p><p>Cas tilts his head. “I… would say it depends on your perspective and what you value. Luke may not have been in constant danger, but he was very alone. He was not a happy man.”</p><p>There’s silence for a moment, and Kevin purses his lips. “Was his family safe?”</p><p>Cas gives Kevin a sad smile. “He had none. His mother and father both passed away before his activation as a Prophet of the Lord.” </p><p>The guilt is gnawing away at Dean again. Kevin looks prepped to ask another question, so Dean decides enough is enough. “Okay, okay,” Dean interrupts. “That’s bending the rules. One question at a time, kid.”</p><p>***</p><p>“Dean, Truth or Dare.”</p><p>“You know me, Sammy,” Dean says, taking a sip of his beer and wiggling his eyebrows.</p><p>“So, dare, then?” Sam’s got a sinister-looking smile on his face, and it’s growing. Dean is beginning to think that maybe, just maybe, he should be a little bit afraid.</p><p>“Of course,” Dean replies aloud, though, because he’s not backing down.</p><p>“Alright, then.” Sam leans forward, smirking. “I dare you to only eat veggie burgers for a month.”</p><p>Dean’s jaw drops. This is somehow worse than he was expecting. “What? That’s not—you can’t extend the time—”</p><p>“And where was that rule when last time you made me wear that glitter fanny pack you found at school for a month?”</p><p>Dean glares. Sam has a point, so it’s up to saving face now. “Fine,” he spits. “It won’t be a problem.”</p><p>Sam just smiles knowingly.</p><p>Dean looks down at his hot dog, which he’s only halfway through, and suddenly cherishes the fact that at least it’s meat.</p><p>***</p><p>“Sam, Truth or Dare.”</p><p>Sam sizes Cas up, then decides, “Dare.”</p><p>Cas cocks his head, and, without missing a beat, says, “I dare you to tell the couple outside that you are a platypus.”</p><p>There’s an incredulous silence. Sam’s mouth is hanging slightly open. “Why… a platypus?”</p><p>Cas doesn’t blink. “I like them. They are strange creatures.”</p><p>They all make the field trip outside to talk to the poor, unsuspecting passerbys. It goes about as well as expected, although mercifully for Sam, Dean and Kevin’s snickers probably alert the couple to the fact that some kind of prank is being pulled. Still, Dean eyes Cas’s quiet smile at the ensuing hijinks. He’s starting to get the hang of what a dare means, and sure, it was silly, but it was damn creative. Cas may have a long way to go, but his attempts are…  adorable. And the fact that he’s doing it all stone cold sober while the rest of them get drunker and drunker is downright admirable.</p><p>Cas is also unpredictable, and he’s learning fast. Dean may… actually have to be on guard when it’s Cas’s turn to Truth or Dare him.</p><p>***</p><p>On second thought, he forgot about Kevin. The kid’s way worse. Waaaay worse.</p><p>“I dare you to get frosted tips.”</p><p>Sonuvabitch.</p><p>***</p><p>Hair bleach is <em>really</em> not easy to use. It comes out all lopsided (especially with Sam and Kevin “helping.”) Dean swears he’s going to find a way to dye it back before tomorrow’s over.</p><p>***</p><p>Kevin’s not any easier on Sam when it’s Sam’s turn. “I dare you to dress up as your worst ex-girlfriend and spend the rest of the night doing your best impression of her.”</p><p>Dean does the good old point-and-laugh. “Ruby! It’s gotta be Ruby.”</p><p>There’s a glint of terror in Sam’s eyes. “Oh, no, not her, no way.”</p><p>Cas transports them all to the nearest Goodwill. Dean doesn’t know how they manage it, but they scrounge up enough skanky clothes in Sam’s size (and a nice, horrid wig the right color) to do the trick. </p><p>Then Dean insists on makeup. (None of them know how to apply the stuff, but that makes it all the better.) By the time they’re done, Sam’s lips are a gaudy dark red and his eyes look like a raccoon’s. </p><p>Unfortunately, Sam’s a terrible enough actor that some of the fun drains away when he tries to get in character, but by that point, Dean’s had plenty of rounds of raucous laughter at his expense.</p><p>Sam’s eyes speak of revenge. And unfortunately, it’ll be easier for him to stay in character that way. Ruby always was a vengeful little bitch.</p><p>***</p><p>“Truth or Dare, Cas.”</p><p>“Dare,” Cas says.</p><p>Dean grins. “I dare you to kiss a frog.”</p><p>Cas tilts his head in confusion. Then, he’s gone, and he’s back barely a moment later with a small, disgruntled-looking frog. Without delay, he gives it a no-nonsense peck on the back, and before Dean can cry foul and claim that it wasn’t on the lips, Cas disappears to put the frog back again. The whole thing is over in a matter of seconds. When he shows back up, Dean stares at him. Does nothing faze the guy?</p><p>“What?” Cas frowns. “Did I not kiss the frog correctly?”</p><p>Dean sinks into his chair and rubs his forehead. “Damn it, Cas.”</p><p>Kevin and Sam giggle in the background.</p><p>***</p><p>Dean doesn’t understand. Isn’t Sam’s revenge supposed to be on Kevin, not him?</p><p>“Look,” Sam says in a half-assed falsetto, “it’s uh, not my problem if you don’t have the guts to pull it off.” He lifts his right hand and pretends to check his nails disinterestedly.</p><p>Okay, on second thought, Sammy is starting to get better at being in character, and right now, it’s not even funny anymore.</p><p>“No way. It’s Baby, you can’t touch Baby, Sammy—sorry, uh, Ruby.”</p><p>Sam-as-Ruby rolls his eyes dramatically. “I swear, you and that car have more sexual tension than you and any of your previous girlfriends. Get a room.”</p><p>Dean wants to scream.</p><p>Kevin’s doing a poor job of hiding his giggles, and even Cas is smiling, the <em>traitor.</em></p><p>“You could always do Truth instead,” Sam drawls. “Oh, that’s right, I forgot. You’re too—”</p><p>“Okay, okay, okay!”</p><p>The iPod gets reinstalled into Baby.</p><p>***</p><p>Dean thinks he might be starting to lose his touch. Clearly, he misjudged something about Kevin’s sense of humor and his hidden talents, because the goddamn kid’s enjoying this—and Dean most certainly is <em>not.</em></p><p><em>“Friday, Friday, Gotta get down on Friday,”</em> Kevin sings, his voice somehow a near-perfect match of Rebecca Black’s. He’s hamming it up and grinning like a loon.</p><p>Dean narrows his eyes. Goddamnit, he’ll think of something.</p><p>***</p><p>“Cas, Truth or Dare.”</p><p>Cas pauses for a moment this time. “Truth,” is the quiet answer.</p><p>Dean watches him, then takes a sip of beer. He’s got that face on, the one that means he’s thinking about something far too serious for this silly night. For heaven’s sake, Sam is in drag, Kevin’s sung falsetto, and Dean now has frosted tips <em>and</em> is wearing <em>Putin’s underwear.</em> This was supposed to lift Cas’s spirits, too.</p><p>Naturally, that means Dean asks him the silliest question he can think of.</p><p>“If you had to pick a pagan god,” Dean starts, “who would you—”</p><p>“Oh, come on,” Kevin interrupts. “You always do the same damn question, every time.”</p><p>Dean splutters. “It does the trick!” He finds himself turning subconsciously back to see Sammy’s reaction. </p><p>“Don’t look at me,” Sam-as-Ruby says, tossing his polyester hair. “You always were rather unimaginative.”</p><p>Right. No help there.</p><p>Dean turns back to Cas. “Uh… well? Who would you—”</p><p>“Athena,” Cas interrupts, face unreadable. “I got along with her quite well back in the fifth century, actually.”</p><p>Dean stares. </p><p>“Uh… well… good for you.” </p><p>Suddenly feeling deflated, Dean takes a long swig of his beer.</p><p>***</p><p>Dean feels a little better when Cas, of all people, manages to throw Kevin a curveball.</p><p>“You want me to… what?” Kevin’s jaw is hanging open in disbelief.</p><p>“Paint the statue of Robert E. Lee in Richmond, Virginia neon pink. Was I not clear enough? I was under the impression that causing harmless shame to distasteful figures was encouraged, and that the color neon pink was considered to be the most embarrassing. I’d provide the paint and the transportation, of course—”</p><p>“No, no, I’ll do it. Just…” Kevin sucks in a breath. “Okay. This one is a little… riskier.” </p><p>Dean moves around to give Kevin a too-hard pat on the back. “Whatcha worried about, Picasso? You have us as backup.”</p><p>Kevin gives him a wilting look.</p><p>In the end, Kevin comes up with the idea that can get them in and out the safest. With Cas’s help, he manages to commandeer some sort of crane and hang a concerningly large vat of neon pink paint above the statue, before dumping it, all at once. Dean’s exhilarated, watching it all splash down, at first, but then the splatters fly everywhere. Sammy gets some in his wig. Dean’s best boots are ruined. At least the statue looks like a glorious, pink mess.</p><p>“Cas, could you, uh, clean us up, please?”</p><p>“Oh. Ah, right. The paint.” Cas glances down at his trenchcoat and magics it clean. “I forgot about that.”</p><p>Dean pinches the bridge of his nose. “I meant us, too, Cas.”</p><p>Cas tilts his head, but it’s an overly exaggerated motion this time, in the way that lets Dean know he’s going to be a little shit on purpose. “I believe you explained the objective of Truth or Dare is to cause the most embarrassment for others while preserving yourself. As the pink paint seems to cause you shame, I would be acting against my best interest to spare you.”</p><p>Sam-as-Ruby gives an exaggerated shrug. “I mean, he’s not wrong.”</p><p>Kevin, who was spared most of the spatters, grins.</p><p>Dean groans.</p><p>***</p><p>Is Sammy trying to kill him? Dean swears, Sammy’s trying to kill him. His dares are getting harder and harder.</p><p>Sam shrugs, but he’s got a wicked smirk on his face. “If I have to be in drag, I might as well <em>drag</em> you down with me.”</p><p>“Hey!” Kevin exclaims, snapping his fingers at Sam. “That was out of character. You’re not Sam, you’re Ruby. <em>Ruby,”</em></p><p>Sam immediately shifts his posture, crossing his arms and jutting his hip out in a distinctly feminine manner, but his eyes say, <em>case and point.</em></p><p>“Yeah, but—Sammy, <em>video evidence?</em> We swore years ago that was against the rules.”</p><p>“Yeah, well, that didn’t stop you from recording me—” Sam catches Kevin’s eye and clears his throat. “Sorry, <em>Sam,</em> when you made him ask a clown for a piggyback ride at Plucky’s.”</p><p>Damn it, Sam’s got him there. <em>Again.</em> </p><p>“Truth’s still an option, you know—“</p><p>Which is how Dean ends up dressed in drag, in what is supposed to be a vague semblance of Britney Spears, singing “Oops, I Did It Again” while attempting to pole dance in <em>heels.</em> And Sam’s recording. The whole time.</p><p>Dean… sort of has fun, though, even if Dean would <em>never, ever</em> admit it. He’s starting to get why Kevin enjoyed the Friday dare. Dean likes hamming it up and being funny, okay? And this definitely tickles his funny bone. </p><p>That doesn’t mean he isn’t infinitely grateful for the chance to change back into his paint-splattered clothes and Putin’s undies, and <em>man,</em> that was not a sentence he ever expected to say, even in his head.</p><p>He is going to have such a big hangover tomorrow.</p><p>***</p><p>When it’s his time to get Sammy back, the little bitch says “Truth” instead of “Dare.” </p><p>Dean scowls, and his tongue’s just loose enough that he fires back, “Okay, then, who was better in bed: Ruby or Jessica?”</p><p>Sam blinks at him in shocked silence for a moment, and Dean can feel the atmosphere in the room still. Oh God, he just crossed a line, didn’t he—</p><p>—but then Sam shifts back into his godawful Ruby character and says, “I knew more tricks, but… he always enjoyed it more with Jessica, because she had his heart, the way I never could.”</p><p>Dean smiles.</p><p>***</p><p>Finally, <em>finally,</em> Cas picks Dean for Truth or Dare. Dean hadn’t fully realized how curious he was to see how it would turn out.</p><p>“Dare,” he responds, because <em>duh.</em></p><p>“I dare you to catch a squirrel.”</p><p>Dean blinks. “What?’</p><p>Cas smiles at him, faux-innocent. “They are rather… swift creatures. I’m merely curious to see how you might catch them.”</p><p>“But… that’s got to be impossible. And aren’t they all asleep by now?”</p><p>“Finding the squirrel should be no trouble for me. I’m just asking that you catch it.”</p><p>Dean shoots Sammy a <em>can you believe this guy?</em> look, but he and Kevin are too busy snickering.</p><p>“Uh… alright?”</p><p>Dean steals some fishermens’ gear from the docks to use as a makeshift trap. Cas transports them to the nearest park, where he has apparently located enough squirrels to chase. </p><p>It takes him over an hour before it works, and pretty much only by a fluke. Dean sits on the park grass, holding the end of his makeshift net tight to keep the squirming squirrel from escaping, and pants. </p><p>“Hey guys,” he starts. “Uh… what do you say we make this the last round.”</p><p>“Oh, I’m not tired at all,” Kevin puts in, the smartass.</p><p>“Come on, Dean, one more round,” Sam-as-Ruby purrs.</p><p>Dean looks around. He’s outvoted. “Alright,” he acquiesces, then staggers to his feet. “Let’s get this show on the road,” he says, trying to summon some enthusiasm, because he still has his pride to think about.</p><p>“Wait,” Kevin says. “What should we name it?”</p><p>Dean blinks in confusion, before he remembers. “The squirrel?”</p><p>“I’ll ask,” Cas says, deadpan, and leans over to stare at the squirrel, which is still clearly terrified, limbs and claws flailing in every direction. At Cas’s approach, however, it stills.</p><p>Cas stares at the squirrel for a few moments, then nods and straightens. “She says her name is Almalathia.”</p><p>Dean’s so drunk and tired he can’t even tell whether or not Cas is kidding.</p><p>***</p><p>Dean manages to mortify Kevin a little when he pries out the story of how he asked out his first crush (there was honest-to-god tripping and gum-in-hair involved). Kevin teaches Cas the Hokey-Pokey and has him surprise an angel buddy of his with it, and Cas makes Sam tell everyone he keeps his hair long because he thinks it makes him look hot. (Cas’s original question just seemed to be out of curiosity, but since Cas has been getting the hang of the game, Dean can’t tell how innocuous the question really was.) But then it’s Sam’s turn, and he’s smirking.</p><p>Dean's stomach drops. Sam's plotting something.</p><p>“Truth or Dare, Dean,” Sam-as-Ruby drawls, batting his eyelashes (and God if that wasn’t getting annoying).</p><p>“Dare,” Dean spits testily.</p><p>Sam looks like the cat that ate the canary.</p><p>“I dare you to summon Crowly and kiss him on the lips.”</p><p>Dean gapes, the wind knocked right out of him.</p><p>Wait. The veggie burgers, the iPod in his Baby, the Britney Spears stripper dance… he thinks he gets Sam’s game now. He’s trying to get him to say ‘truth,’ which means he’s got something <em>much</em> worse planned for that. He’s trying to get him to crack, to decline a dare. Out of the frying pan and into the fire.</p><p>But then Kevin pipes up, and Dean nearly takes a step back at the sheer rage on the kid’s face. “No. No way. You do <em>not</em> get to use him in the game.”</p><p>It’s like a bubble has burst. Dean and Cas are frozen, and the smile leaves Sam’s face. “Kevin—” Sam starts.</p><p>“We’ve crossed a lot of lines tonight, okay, but that is the one I will not—”</p><p>“I’ll do it,” Dean interrupts.</p><p>Kevin whirls on him. “Are you out of your mind?”</p><p>He winces at the look on the kid’s face… but his pride is at stake. “We’ll go to a warehouse halfway across the country. You’ll stay warded and safe.”</p><p>Kevin’s face is stony. “I can’t believe you.” He rounds on Sam and Cas. “All of you. I thought you were smarter than this, that you <em>cared</em> more than this. You’re willing to put lives in actual danger because of a stupid <em>game?”</em> Kevin turns back to Dean. “And you—” he scowls. “Are you willing to do something that reckless just to avoid telling the goddamn <em>truth?”</em></p><p>There’s a heavy silence in the air. Kevin’s right—and they should have stopped this even before, stopped the drunken escalation before it went too far. </p><p>“Fine,” Dean says. “Truth.”</p><p>Sam looks conflicted, as though having the fun drained out of the game is making him hesitant to go through with what he planned—but then a determined look replaces his uncertain one. “If you had to marry anyone today, who would you pick?”</p><p>Dean’s too drunk and worn-down to do anything but admit the first thing that comes to his mind, to get it over with. “Cas,” he says.</p><p>Next to him, Cas stills, his eyes going wide. At the look on his face, Dean’s mind starts frantically backpedaling. “Well, I mean, if you’re going to spend the rest of your life with someone, better choose your best bud—I mean—”</p><p>Cas is still gaping at him in shock.</p><p>“I can’t believe this shit,” Kevin says, throwing up his hands, and he stalks out of the room. Dean and Cas watch him go. Sam’s still too busy studying the two of them, a suspiciously satisfied look on his face. </p><p>“Well,” Dean says, to fill the uncomfortable silence. “I guess we’d better hit the hay—”</p><p>“I’d marry you too,” Cas blurts, and now Dean’s the one who’s speechless. “If I had to marry anyone today, of course.”</p><p>Dean’s brain must be more out of it than he thought, because he could have sworn that sounded like Cas was into him.</p><p>“Wow, uh, thanks,” Dean says, stupidly. Then he grabs his duffel and practically runs to the Impala. </p><p>The ride home is silent and awkward as all hell, and Dean’s grateful when they’re back at their motel. The clock on Dean’s nightstand says it’s 4 AM.</p><p>Well, no wonder he’s so tired. Dean hates to admit it, but his capacity to stay up half the night is diminishing with age.</p><p>Avoiding both Cas, staring in that questioning way of his, and Sam, still dressed as Ruby but making far too meaningful faces at him, Dean flops on his bed and welcomes oblivion.</p><p>***</p><p>They drop in on Kevin the next day to help him clean up—and to get the information they came here for in the first place. At first, the kid’s too grouchy and hungover (even though Dean barely saw him drink all night, the lightweight) to talk to them much, but then—</p><p>“Wait, hold on,” Kevin says, rummaging through a pile of various crap in the corner. “Is that—the squirrel?”</p><p>Dean and Sam look up from their own attempts at organizing Kevin’s slovenly things. Dean holds back a laugh. The kid isn’t kidding. The squirrel he caught last night is somehow buried in the corner, in a cage that looks better suited to a bird than a mammal.</p><p>“Ah, Almalathia,” Cas greets with a solemn nod. “Good to see you.”</p><p>The caged squirrel declines to respond. </p><p>“Oh my God,” Kevin chuckles softly, shaking his head. “I can’t believe that’s still here. We should—we should really let her out.”</p><p>“Wait,” Sam says, with an air of dawning realization. “We should check the news in Richmond, Virginia.”</p><p>Dean shoots him a blank look, but Cas smiles. “Ah yes, the statue.”</p><p>Sonuvabitch, Dean nearly forgot.</p><p>Kevin’s face lights up like a Christmas tree, and they all hurry to draw in close as Sam pulls up the search results on his computer.</p><p><em>A Study in Pink: Mysterious Vandals Wash Richmond’s Robert E. Lee Statue in Color,</em> the first headline blares. </p><p>“Oh my <em>God,”</em> Kevin repeats, emphatically, before collapsing into a fit of giggles. </p><p>“Get this,” Sam says in his Incoming Research Nerd-Out voice. “People have been posing for photos in front of it, tagged: <em>GetPink’dYouDeadConfederate.”</em> </p><p>“Wait, lemme see,” Dean buts in, dragging the computer in his direction.</p><p>The photos don’t disappoint. The statue, as well as its immediate surroundings, are absolutely <em>drenched</em> in the blinding color, and people are doing their best to show their complete and utter lack of respect. Some crouch with peace signs and sunglasses. Others do ridiculous dance moves.</p><p>“Dude,” Dean says, absolutely beaming at their handiwork. He looks up to find Cas. “Cas, you are a <em>genius.</em> Next time I play Truth or Dare, I sure as hell want you there.”</p><p>Cas stares at him like he’s made his day. Dean looks away, suddenly uncomfortable. </p><p>A giggle sounds to his right, and Dean whirls around to see Kevin and Sam huddled over something. Dean’s radar immediately starts pinging—and sure enough, to his utter mortification, it’s the Britney Spears stripping video.</p><p>“Hey!” Dean barks. He makes a grab for Sam’s phone, but his brother snatches it out of reach, laughing. The whole scramble for the phone ends up with the two wrestling on the floor, just like old times. Dean never does manage to get his hands on the phone, but Sam stops the video out of pity.</p><p>When they’ve both brushed themselves off and risen to their feet, Kevin approaches them, face serious this time, fidgeting slightly. “Look, despite how it ended last night—I wanted to say thank you. My birthday… didn’t actually suck because of you.”</p><p>“Well, no problem, Kev,” Dean says, and then lets out a surprised “oof” when the kid pulls him in for a hug. </p><p>“You were right, it did help,” Kevin murmurs. “Payback.”</p><p>Dean lets Kevin hug him longer than he usually would, a warm and fuzzy feeling forming in his chest that feels suspiciously like <em>family.</em></p><p>***</p><p>Dean, Sam and Cas take over to work the demon case that had gotten Cas involved in the first place. It goes about as well as they could hope, considering, well, <em>demons,</em> but the demons they encounter end up dead and everyone comes out with their limbs intact, so Dean counts this as a win.</p><p>Then comes the part where they all trudge back to the Impala, and Dean’s suddenly hit by the realization that this is where Cas usually says his goodbyes. He stops in his tracks and peers at Cas, and sure enough, the dude looks like he’s about to bolt. But there’s something about the discomfort in his posture that tells Dean he doesn’t want to go, not really.</p><p>Dean watches him, discomfort forming in his gut.</p><p>Ah, screw it.</p><p>“Cas,” Dean calls. “Wait up, buddy.”</p><p>Cas does as Dean asks, looking like he doesn’t know what to expect.</p><p>Dean swallows. “Cas… you can stick around, if you want to.”</p><p>Cas frowns. “But… you’re about to go hunting.”</p><p>Now it’s Dean’s turn to be confused. “Well, yeah, uh, and we could use some backup.”</p><p>“I thought you said I was terrible at hunting,” Cas says carefully, and it hits Dean like a punch to the gut. Oh God, Cas thinks they don’t want him around.</p><p>“No, God no, I meant—“ Dean pinches the bridge of his nose. “It’s like… Truth or Dare.”</p><p>Cas tilts his head. “What is?”</p><p>“Uh, hunting,” Dean says. “See, with Truth or Dare, it took you a little bit to learn the ropes, but then once you got it, you were a genius at it, in your own little… weird… angel way. I’m sure, with a little more time, it would be the same way with hunting.”</p><p>Cas stares at him for a couple moments more, still uncertain.</p><p>“So…” Dean finishes, dropping his hands to his sides helplessly. “You can come with us, if you want.”</p><p>“Do you want me with you?” Cas inquires. He sounds hopeful. </p><p>Alright… Dean’s had enough of this chick-flick moment by now. He slaps Cas on the back. “I said I’d marry you, didn’t I?”</p><p>Cas chokes.</p><p>“Hey, you coming?” Sam calls from the Impala.</p><p>“Yeah,” Dean shouts back. He glances at Cas. “We both are.”</p><p>Sam smiles.</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>I like to think that later, Dean loses a bet to Sam and ends up really going through with the Crowley dare. They don't tell Kevin, or Cas, both for obvious reasons, but Sam still has photo evidence.</p></blockquote></div></div>
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